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CHAPTER 2

Asymmetric Domino Reactions Based on the Use of Chiral Metal Catalysts

This chapter illustrates how much asymmetric organometallic catalysis has contributed to the development of enantioselective domino and multicomponent reactions. It updates the major progress in the field of enantioselective one-, two-, and multicomponent domino reactions promoted by chiral metal catalysts. It is divided into two parts, which deal with one- and two-component domino reactions, and multicomponent reactions, respectively. The first part is subdivided into 12 sections, dealing successively with domino reactions initiated by the Michael reaction, domino reactions initiated by an aldol reaction, domino reductive aldol reactions, domino reactions initiated by a [2+2+2] cycloaddition, domino reactions initiated by an allylic alkylation, domino Passerini-type reactions, domino carbonyl ylide-formation—1,3-dipolar cycloaddition reactions, domino reactions initiated by the Heck reaction, domino reactions initiated by the Wacker reaction, domino reactions based on cyclisations, domino radical reactions, and finally miscellaneous domino reactions. The second part of the chapter, which concerns the multicomponent reactions, is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by a pericyclic reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions initiated by the Friedel—Crafts reaction, multicomponent reactions of alkynes, aldehydes and amines, multicomponent reactions of 1,3-dienes, aldehydes and reducing agents, multicomponent reductive amination reactions of ketones, multicomponent Kabachnik—Fields reactions, and finally miscellaneous multicomponent reactions. This chapter demonstrates the economic interest in combinations of asymmetric metal catalytic processes, with the concept of domino and multicomponent reactions. These allow attainment of high molecular complexity with often high stereocontrol through simple operational one-pot procedures, and advantages of savings in solvent, time, energy, and costs. The wide variety of these fascinating domino reactions reflects that of the metals employed to induce them. Indeed, an increasing number of different metals such as magnesium, scandium, titanium, ruthenium, cobalt, rhodium, iridium, nickel, palladium, platinum, copper, silver, gold, zinc and aluminium, as well as tin, have been found to be effective catalysts.

Print publication date: 13 Mar 2013
Copyright year: 2013
Print ISBN: 978-1-84973-651-0
PDF eISBN: 978-1-84973-710-4
Citation:
From the book series:
Catalysis Series